http://www.neveh.org/felman/felman-vayachee64.html.
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The Gemmoro in Avodah Zarah 11b relates that the Roman Empire is accustomed to the following. Once every seventy years, they take a healthy man and place him on top of a lame man, clothe him in the garments of Odom Harishon, place on his head the skin of the face of Reb Yishmoel (Reb Yishmoel ben Elisha, the Cohein Gadol), adorn his neck with two hundred zuzim of precious stones and spread those stone in the streets. When they have finished setting the stage, they parade them through the streets. They call in front of them, “The promises that Yaakov promised his children (the reference is to Parshas Vayechi in which Yaakov calls his children together to reveal to them what will transpire in the end of days) were false. The brother of our master is a fraud! What did he benefit from all his trickery?” These are just some of the goings on at this parade. What the Romans were obviously depicting is the state of when Yaakov represented by the lame man, finds himself subservient to Eisav represented by the man on top. He has control of the whole world, the clothes of Odom Harishon, riches etc. However what is quite intriguing is what is possibly the meaning of taking the skin of the face of Reb Yishmoel and adorning the face of Eisav with that skin. What could that possibly represent? Aside from that, maybe we can possibly shed light why was it that Reb Yishmoel was the one that received this most cruel punishment of having the skin peeled off his face.
Let us begin by expounding somewhat on the story of the “Asara Harugei Malchus” “The Ten Martyrs” as related in the Medrash Aileh Ezkara. (This Medrash can be found in the more recent publications of the Kinnos of Tisha Baav.) The Medrash relates how the Caesar was studying the Torah and came across the sale of Yoseif by his brothers. The Medrash raises the following query. If Yoseif was so beautiful (the Torah goes out of its way to describe the beauty of Yoseif) why is it that the brothers were able to receive merely twenty coins for Yoseif as a slave? The Medrash reveals something fascinating based on the teachings of the Gemmoro in Shabbos. When the Torah points out that there was no water in the pit that his brothers threw Yoseif into, we are being hinted to that there were snakes and scorpions in the pit. When Yoseif saw this he became so frightened, that the beauty of his face left him. Ha-shem made sure that he was saved and he ultimately ended up down in Egypt. The Medrash relates that the Rabbis were summoned and were told that since the transgression of kidnapping and selling a fellow Jew is punishable with death, being that the brothers were never punished for their deeds, the rabbis would need to stand in their stead and receive the punishment. They asked for three days. In the meanwhile the smallest amongst them, Reb Yishmoel Coheine Gadol volunteered that if they are willing to share with him the punishment of uttering Ha-shem’s name in vein, he would be willing to go up to the heavens and see if this decree was acceptable above. If it was the will of Ha-shem, they would accept it. If not, they would annul it by the use of one of the Holy Names. Here the Medrash goes off onto a tangent as to the birth of Reb Yishmoel. It seems that the mother of Reb Yishmoel would constantly give birth to sons and they would inevitably die. Reb Elisha the Cohein Gadol suggested to his wife that they accept upon themselves a certain resolution in matters of modesty. Later when his wife immersed herself in the mikveh, when she came out she saw a pig. She immersed herself once again and she saw a leper. She immersed again and saw a camel. (All of the above are impure.) At that point Hakadosh Boruch Hu told the great heavenly angel, Metat-ron, that he should go stand in front of this woman in order that she should gaze upon him upon her exit from the bathhouse. He went down and stood on one side and the heavenly angel Gavriel stood on the other side adorned in beautiful clothes. She saw Gavriel and went home and that night Reb Yishmoel was conceived and he was as beautiful as Gavriel. Interestingly enough, whenever Reb Yishmoel would utter the Name of Ha-shem, a special wind would come and whisk him up to the sky and Gavriel would meet him and fulfil all his needs. In the Piyut that we recite on Yom Kippur, it seems that it was Gavriel that was of assistance to Reb Yishmoel when he rose to the heavens at this junction to investigate what the heavenly opinion was as far as this decree. Reb Yishmoel was informed that indeed the will of Ha-shem was that the decree should be accepted and they should not try to put a stop to its being carried out.
In describing the executions of the Ten Martyrs, the Medrash says that Reb Yishmoel was one of the even most beautiful men that ever lived. They are Odom Harishon, Yaakov, Yoseif, Shaul, Avshalom, Reb Avahu and Reb Yishmoel. When Reb Yishmoel was brought to Rome all the women that saw him menstruated. When he was brought to the Caesar, the Caesar asked him if there is anyone as beautiful as he is in the nation to which Reb Yishmoel replied in the negative. There was then the well-known question of who would be killed first Rabban Shimon ben Gamliel, the Nasi, or Reb Yishmoel. They drew lots, which fell on Rabban Shimon ben Gamliel. After he was executed, it came the trn of Reb Yishmoel. When the daughter of the Caeser beheld the beauty of Reb Yishmoel she desired him. It was said, the Medrash continues that from the time of Yoesif there hadn’t been anyone as beautiful. She requested that his life be spared. Her request was denied. She continued and asked that at the very least, let the skin off his face be stripped and that it should be given to her. This request was fulfilled. The Medrash than goes on to discuss the circumstances of his death and the other Martyrs.
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